Preheat oven to 400 degrees F. Place the cut garlic bulb on a piece of aluminum foil and drizzle with olive oil. Close the packet and bake in the oven for 40 minutes until softened. Put the cut potatoes in a large stockpot, cover with cold water, and add salt. Bring to a boil, then simmer until the potatoes are fork tender, about 20 to 30 minutes. Drain well in a colander. While the potatoes are still warm, press them through a potato ricer or food mill and into a mixing bowl. Whip in the warm milk and softened butter until incorporated and the potatoes are fluffy. Squeeze the roasted garlic cloves out of the skins. Add the garlic pulp to the potatoes. Beat again; season with salt and pepper.
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